The present invention relates to acrylate ester ethers, processes for their production and isolation, and their use in bulk and solution polymerization. The invention has particular application as cross-linking agents for polymers.
Reaction of methyl acrylates with various aldehydes in the presence of 1,4-diazabicyclo-[2.2.2]-octane (DABCO) has been reported by H. M. R. Hoffmann and J. J. Rabe, 50 J. Org. Chem. 3849 (1985). Lower members of this series have been used previously as synthons in natural product synthesis. Hoffmann and Rabe did not describe, however, products produced when methylacrylate is reacted with formaldehyde. One such product, ethyl alpha-(hydroxymethyl) acrylate was synthesized by a Wittig-Horner reaction of triethylphosphonoacetate by J. Villieras and M. Rambaud, Synthesis, p. 924 (1982). Like the Hoffmann and Rabe publication, the Villieras and Rambaud article did not describe the preparation of the products of the present application.
European application number EP 0,184,731 discloses the preparation of 2-1-hydroxy-methyl-acrylonitrile or acrylic acid ester derivative by reacting acrylonitrile or acrylic acid ester with hydrated formaldehyde or formaldehyde semi-acetal using a tertiary amine catalyst such as 1,4-diazabicyclo-[2.2.2]-octane, pyrrocholine or quinolidine. However, this application does not disclose the formation of any ethers.